N-bromobutanimide → HCID 25258089, compound

HRID 505803Notes

Reaction equation

HRID 505803 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:26])C(=O)C1>C(Cl)Cl>[Br:26][C:13]1[S:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]=1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68467869HCID 68467869, compound

Product 1

HCID 25258089HCID 25258089, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution (0.2 M) of ethyl 4-[(tert-butoxycarbonyl)amino]thiophene-2-carboxylate in DCM was cooled to 0° C. and treated with NBS (1.1 eq.) then stirred at 0° C. for 30 min. The mixture was quenched with aqueous Na2S2O3 (saturated solution) and extracted with AcOEt. The organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine then dried and concentrated. The residue was purified by flash chromatography on silica gel (1:12 AcOEt/petroleum ether) to afford the title compound (48%) as a solid. 1H NMR (300 MHz, DMSO-d, 300 K) δ 1.32 (t, J=7.07 Hz, 3H), 1.50 (s, 9H), 4.32 (q, J=7.07 Hz, 2H), 7.81 (s, 1H), 9.13 (bs, 1H); MS (ES+) m/z 350, 352 (M+H)+;

Workup

  1. customThe mixture was quenched with aqueous Na2S2O3 (saturated solution)
  2. extractionextracted with AcOEt
  3. washThe organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine
  4. customthen dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (1:12 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-2425ec2d8f2748e58105e4bac62191ba
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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